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1.
J Food Sci Technol ; 60(2): 453-463, 2023 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-36712201

RESUMO

A new methodology was developed to print pizza dough with a gluten free flour blend or commercial gluten whole wheat flour using extrusion-based 3-D printing technology. Their physical properties were compared to commercially available pizza dough and crust. The optimized nozzle size, print speed, ingredient flow speed, and line thickness for the 3-D printing of pizza dough were: 0.04 cm, 800 cm/minutes, 1.8, and 0.34 cm, respectively. The printed gluten-free pizza dough required 120 min of fermentation to obtain a comparable color and textural profile (P < 0.05) to that of the gluten whole wheat flour dough fermented for 60 min. The 3-D printed gluten free, whole-wheat pizza and commercially available wheat flour dough and standard crusts demonstrated identical Δ E ab ∗ values of 0.14 and 0.13, respectively with brownness index (BI) values of 1.47 and 1.62, respectively. Textural profile analysis (TPA) of 3-D printed gluten free and whole wheat pizza dough, crust and the commercial standard wheat flour pizza dough and crust demonstrated significant (P < 0.05) correlations in terms of hardness, fracturability, adhesiveness, springiness, cohesiveness, chewiness, and resilience. An optimized method was developed to prepare gluten-free pizza dough and crust with similar functional properties to that of gluten whole wheat flour dough and crust.

2.
Bioorg Med Chem ; 22(17): 4935-47, 2014 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-25088548

RESUMO

As part of our ongoing efforts to identify compounds having potential utility in treating neurodegenerative and mitochondrial disorders, a series of pyridinol analogues have been prepared. The synthetic route employed for the preparation of the new analogues is different, and considerably more efficient, than that used in previously reported studies. The new route yields a pair of pyridinol regioisomers that can be readily separated and evaluated. Their ability to quench lipid peroxidation and reactive oxygen species (ROS), and to preserve mitochondrial membrane potential (Δψm) and support ATP synthesis is reported. The optimal side chain length was found to be 16 carbon atoms. The metabolic stability of those compounds having optimal biological activities was evaluated in vitro using bovine liver microsomes. The omission of any side chain hydroxyl group and introduction of an azetidine moiety at position 6 of the pyridinol redox core (8 and 9) increased their microsomal stability as compared to the exocyclic dimethylamino group. The favorable metabolic stability conferred by the azetidine moiety in compounds 8 and 9 makes these compounds excellent candidates for further evaluation.


Assuntos
Antioxidantes/farmacologia , Citoproteção/efeitos dos fármacos , Doenças Mitocondriais/tratamento farmacológico , Doenças Neurodegenerativas/tratamento farmacológico , Fármacos Neuroprotetores/farmacologia , Piridinas/farmacologia , Animais , Antioxidantes/síntese química , Antioxidantes/química , Bovinos , Células Cultivadas , Relação Dose-Resposta a Droga , Humanos , Peroxidação de Lipídeos/efeitos dos fármacos , Linfócitos/efeitos dos fármacos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Microssomos Hepáticos/química , Microssomos Hepáticos/metabolismo , Doenças Mitocondriais/patologia , Estrutura Molecular , Doenças Neurodegenerativas/patologia , Fármacos Neuroprotetores/síntese química , Fármacos Neuroprotetores/química , Piridinas/síntese química , Piridinas/química , Espécies Reativas de Oxigênio/antagonistas & inibidores , Espécies Reativas de Oxigênio/metabolismo , Relação Estrutura-Atividade
3.
Bioorg Med Chem ; 21(4): 969-78, 2013 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-23313093

RESUMO

Two new aza analogues of the neuroprotective agent idebenone have been synthesized and characterized. Their antioxidant activity, and ability to augment ATP levels have been evaluated in several different cell lines having suboptimal mitochondrial function. Both compounds were found to be good ROS scavengers, and to protect the cells from oxidative stress induced by glutathione depletion. The compounds were more effective than idebenone in neurodegenerative disease cells. These novel pyrimidinol derivatives were also shown to augment ATP levels in coenzyme Q(10)-deficient human lymphocytes. The more lipophilic side chains attached to the pyrimidinol redox core in these compounds resulted in less inhibition of the electron transport chain and improved antioxidant activity.


Assuntos
Antioxidantes/química , Mitocôndrias/metabolismo , Fármacos Neuroprotetores/química , Pirimidinas/química , Ubiquinona/análogos & derivados , Trifosfato de Adenosina/metabolismo , Animais , Antioxidantes/síntese química , Antioxidantes/toxicidade , Bovinos , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Desenho de Fármacos , Glutationa/metabolismo , Humanos , Linfócitos/efeitos dos fármacos , Linfócitos/metabolismo , Mitocôndrias/enzimologia , Complexos Multienzimáticos/antagonistas & inibidores , Complexos Multienzimáticos/metabolismo , NADH NADPH Oxirredutases/antagonistas & inibidores , NADH NADPH Oxirredutases/metabolismo , Doenças Neurodegenerativas/metabolismo , Doenças Neurodegenerativas/patologia , Fármacos Neuroprotetores/síntese química , Fármacos Neuroprotetores/toxicidade , Pirimidinas/síntese química , Pirimidinas/toxicidade , Espécies Reativas de Oxigênio/metabolismo , Ubiquinona/síntese química , Ubiquinona/química , Ubiquinona/genética , Ubiquinona/metabolismo , Ubiquinona/toxicidade
4.
Bioorg Med Chem ; 21(8): 2346-2354, 2013 Apr 15.
Artigo em Inglês | MEDLINE | ID: mdl-23473946

RESUMO

The effect of the alkyl side chain length of coenzyme Q10 on mitochondrial respiratory chain function has been investigated by the use of synthetic ubiquinone derivatives. Three analogues (3, 4 and 6) were identified that exhibited significantly improved effects on mitochondrial oxygen consumption and mitochondrial membrane potential, and also conferred significant cytoprotection on cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate. The analogues also exhibited lesser inhibition of the electron transport chain than idebenone. The results obtained provide guidance for the design of CoQ10 analogues with improved activity compared to that of idebenone (1), the latter of which is undergoing evaluation in the clinic as a therapeutic agent.


Assuntos
Transporte de Elétrons/efeitos dos fármacos , Mitocôndrias/efeitos dos fármacos , Ubiquinona/análogos & derivados , Animais , Bovinos , Linhagem Celular , Linhagem Celular Tumoral , Citoproteção , Transporte de Elétrons/fisiologia , Humanos , Leucemia/metabolismo , Leucemia/patologia , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Mitocôndrias/metabolismo , Consumo de Oxigênio/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo , Células Ganglionares da Retina/citologia , Células Ganglionares da Retina/efeitos dos fármacos , Células Ganglionares da Retina/metabolismo , Relação Estrutura-Atividade , Ubiquinona/química , Ubiquinona/metabolismo , Ubiquinona/farmacologia
5.
Bioorg Med Chem ; 20(17): 5188-201, 2012 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-22883028

RESUMO

Selected pyridinol analogues of the experimental neuroprotective drug idebenone have been synthesized and evaluated as antioxidants capable of preserving mitochondrial function. The compounds, having a different redox core but the same side chain as idebenone, exhibited a range of potencies, reflecting differences in their structures. The results obtained provide guidance in the design of such analogues with improved properties. Analogues were identified that have significantly improved antioxidant activity compared with idebenone in cultured lymphocytes, and which exhibit lesser inhibition of the electron transport chain.


Assuntos
Antioxidantes/farmacologia , Citoproteção/efeitos dos fármacos , Mitocôndrias Cardíacas/efeitos dos fármacos , Piridonas/farmacologia , Animais , Antioxidantes/síntese química , Antioxidantes/química , Bovinos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Peroxidação de Lipídeos/efeitos dos fármacos , Linfócitos/efeitos dos fármacos , Linfócitos/metabolismo , Mitocôndrias Cardíacas/enzimologia , Mitocôndrias Cardíacas/metabolismo , Membranas Mitocondriais/efeitos dos fármacos , Membranas Mitocondriais/metabolismo , Estrutura Molecular , Complexos Multienzimáticos/antagonistas & inibidores , Complexos Multienzimáticos/metabolismo , NADH NADPH Oxirredutases/antagonistas & inibidores , NADH NADPH Oxirredutases/metabolismo , Piridonas/síntese química , Piridonas/química , Espécies Reativas de Oxigênio/antagonistas & inibidores , Espécies Reativas de Oxigênio/metabolismo , Relação Estrutura-Atividade , Células Tumorais Cultivadas
6.
J Food Sci ; 87(11): 4808-4819, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36183162

RESUMO

Increasing market demand for sustainable, environmentally friendly edible film materials has called for the development of new customizable production methods utilizing emerging technologies such as 3D printing. We hereby report a new method to generate functional edible soy protein isolate films prepared from three types of soybeans (AR-R11-7999, MO-S17-17168, and MO-S17-19874R) using an innovative 3D printing technology. The protein contents in AR-R11-7999, MO-S17-17168, and MO-S17-19874R soybean meals and their corresponding protein isolates were 40.0, 39.1, and 39.9; and 84.5, 84.7, and 87.3 % (w/w, dry basis), respectively. Response surface methodology was used to maximize the tensile and puncture strength and minimize the thickness of the 3D-printed edible films using protein concentration, plasticizer concentration (glycerol), and drying time as the independent variables. The optimized film production conditions were determined as soy protein concentration: 8.91%, plasticizer concentration: 3.00%, and drying time: 3.98 h with a desirability value of 0.7428. The optimized conditions were then successfully verified with the original soybean lot with a nonsignificant difference in physical properties. At the optimized conditions, the 3D-printed edible films using three soybean lots revealed: 0.108-0.114 mm thickness; 14.79-16.07 MPa tensile strength; 6.97-8.20 N puncture strength; 90.81-91.53, -1.89 to -1.31, and 14.85-17.25 were color parameters L*, a*, and b*, respectively; 1.22-1.36 g/cm3 density; and 104.4-105.7% elongation at break ratio (%). PRACTICAL APPLICATION: Edible soy protein films produced by an extrusion-based 3D printing approach are highly customizable and precise, and could be produced at an industrial scale. This newly produced environment-friendly soy protein-based edible film can serve as an alternate packaging to synthetic plastics and reduce the environmental landfill problem while adding value to soybean produced in the mid-south United States.


Assuntos
Glycine max , Proteínas de Soja , Plastificantes , Permeabilidade , Resistência à Tração , Tecnologia , Impressão Tridimensional , Embalagem de Alimentos
7.
J Org Chem ; 76(22): 9429-37, 2011 Nov 18.
Artigo em Inglês | MEDLINE | ID: mdl-22011074

RESUMO

The one-pot construction of functionalized α'-methoxy-γ-pyrones is detailed. Starting from α,α'-dimethoxy-γ-pyrone, molecular diversity is attained by a regio- and stereoselective desymmetrization using allyllithium followed by vinylogous aldol reaction. Mechanistic considerations including density functional theory calculations and insightful experiments have been gathered to shed light on this complex multistep process. To illustrate the versatility of this methodology, some of the molecules prepared were evaluated for their ability to inhibit NADH-oxidase and NADH-ubiquinone oxidoreductase. In the process, a potent new inihibitor of NADH-oxidase activity (IC(50) 44 nM) was identified.


Assuntos
Inibidores Enzimáticos/síntese química , Mitocôndrias/efeitos dos fármacos , NADH NADPH Oxirredutases/antagonistas & inibidores , Pironas/síntese química , Pironas/farmacologia , Inibidores Enzimáticos/química , Mitocôndrias/fisiologia , Estrutura Molecular , NADH NADPH Oxirredutases/metabolismo , Pironas/química , Teoria Quântica , Estereoisomerismo
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